AI Spurs More Unicorn Acquisitions As Clio, Grammarly Make M&A Deals
This has been a busy week for unicorns making acquisitions.
On July 1, Canada-based legal software company Clio revealed its plans to acquire Spain’s vLex from Oakley Capital for $1 billion. And, Grammarly — which has been on a buying spree as of late — announced its intent to acquire Superhuman, an AI-native email app.
Clio plans to use cash and stock to fund its purchase of vLex. In a blog post, Clio CEO Jack Newton said the buy is an example of Clio “laying the foundation for the first and only cloud-based, AI-powered platform that seamlessly connects the business and practice of law.”
Founded in 2008, Clio in the past described itself as “the operating system for law firms.” Its software helps law firms automate processes such as client intake, accounting and document management, among other things. It was valued at $3 billion in July 2024 when it raised $900 million in a Series F funding round led by New Enterprise Associates.
As Clio faces greater competition from the likes of 3-year-old startup Harvey, which in June raised a $300 million Series E at a $5 billion valuation, it is clearly trying to get ahead in the legaltech AI race. In his blog post, Newton said: “Now, with our acquisition of vLex, we’re bringing even more to Clio, including extensive legal research and the industry-leading AI known as Vincent.”
Per Crunchbase data, Clio’s planned purchase of vLex so far ranks among the top 10 M&A buys by a unicorn in 2025 so far.
Grammarly makes another move
For its part, San Francisco-based Grammarly said its purchase of Superhuman is “part of the company’s move to become an AI productivity suite.” According to a spokesperson, with the acquisition Grammarly “is bringing agentic AI directly to the inbox.” It follows the company’s January acquisition of Coda, a maker of AI productivity tools.
In a statement, Grammarly CEO Shishir Mehrotra, said the buys are in line with the company’s plans to bring AI “directly to users everywhere they work.”
He added: “Email isn’t just another app; it’s where professionals spend significant portions of their day, and it’s the perfect staging ground for orchestrating multiple AI agents simultaneously.”
The purchase shouldn’t come as a big surprise. When Grammarly announced in late May that it had secured $1 billion in funding from longtime investor General Catalyst, the company said it planned to use its new capital “to scale sales and marketing and for strategic acquisitions.”
When it comes to other unicorns making acquisitions in 2025, the three largest deals involved AI companies so far this year are:
- X (formerly Twitter) was acquired by xAI in a deal that valued X at $33 billion;
- Io was acquired by OpenAI for $6.5 billion; and
- Windsurf acquired by OpenAI for $3 billion.
Overall, there have been 181 acquisitions announced by unicorns in 2025, according to Crunchbase data.
Related Crunchbase queries:
- Unicorn M&A
- Global Venture-Backed M&A
- Venture-Backed M&A Involving US-Based Startups
- Acquisitive Startups
Related reading:
- Legal Tech Startup Clio Raises Whopping $900M At $3B Valuation
- With An Eye Toward More Acquisitions, AI-Powered Grammarly Raises $1B from General Catalyst
- Global M&A Startup Dealmaking Sees Year-To-Year Boost In Q1
- Private Company Purchases By PE Firms Hold Up Amid Market Turbulence
- These Private, VC-Backed Companies Are The Most-Active, Spendiest Startup Acquirers
Illustration: Dom Guzman
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AI Spurs More Unicorn Acquisitions As Clio, Grammarly Make M&A Deals
This has been a busy week for unicorns making acquisitions.
On July 1, Canada-based legal software company Clio revealed its plans to acquire Spain’s vLex from Oakley Capital for $1 billion. And, Grammarly — which has been on a buying spree as of late — announced its intent to acquire Superhuman, an AI-native email app.
Clio plans to use cash and stock to fund its purchase of vLex. In a blog post, Clio CEO Jack Newton said the buy is an example of Clio “laying the foundation for the first and only cloud-based, AI-powered platform that seamlessly connects the business and practice of law.”
Founded in 2008, Clio in the past described itself as “the operating system for law firms.” Its software helps law firms automate processes such as client intake, accounting and document management, among other things. It was valued at $3 billion in July 2024 when it raised $900 million in a Series F funding round led by New Enterprise Associates.
As Clio faces greater competition from the likes of 3-year-old startup Harvey, which in June raised a $300 million Series E at a $5 billion valuation, it is clearly trying to get ahead in the legaltech AI race. In his blog post, Newton said: “Now, with our acquisition of vLex, we’re bringing even more to Clio, including extensive legal research and the industry-leading AI known as Vincent.”
Per Crunchbase data, Clio’s planned purchase of vLex so far ranks among the top 10 M&A buys by a unicorn in 2025 so far.
Grammarly makes another move
For its part, San Francisco-based Grammarly said its purchase of Superhuman is “part of the company’s move to become an AI productivity suite.” According to a spokesperson, with the acquisition Grammarly “is bringing agentic AI directly to the inbox.” It follows the company’s January acquisition of Coda, a maker of AI productivity tools.
In a statement, Grammarly CEO Shishir Mehrotra, said the buys are in line with the company’s plans to bring AI “directly to users everywhere they work.”
He added: “Email isn’t just another app; it’s where professionals spend significant portions of their day, and it’s the perfect staging ground for orchestrating multiple AI agents simultaneously.”
The purchase shouldn’t come as a big surprise. When Grammarly announced in late May that it had secured $1 billion in funding from longtime investor General Catalyst, the company said it planned to use its new capital “to scale sales and marketing and for strategic acquisitions.”
When it comes to other unicorns making acquisitions in 2025, the three largest deals involved AI companies so far this year are:
- X (formerly Twitter) was acquired by xAI in a deal that valued X at $33 billion;
- Io was acquired by OpenAI for $6.5 billion; and
- Windsurf acquired by OpenAI for $3 billion.
Overall, there have been 181 acquisitions announced by unicorns in 2025, according to Crunchbase data.
Related Crunchbase queries:
- Unicorn M&A
- Global Venture-Backed M&A
- Venture-Backed M&A Involving US-Based Startups
- Acquisitive Startups
Related reading:
- Legal Tech Startup Clio Raises Whopping $900M At $3B Valuation
- With An Eye Toward More Acquisitions, AI-Powered Grammarly Raises $1B from General Catalyst
- Global M&A Startup Dealmaking Sees Year-To-Year Boost In Q1
- Private Company Purchases By PE Firms Hold Up Amid Market Turbulence
- These Private, VC-Backed Companies Are The Most-Active, Spendiest Startup Acquirers
Illustration: Dom Guzman
Read More
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